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SML1276

Sigma-Aldrich

BAZ2-ICR

≥98% (HPLC)

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Synonym(s):
4-{4-(1-Methyl-1H-pyrazol-4-yl)-1-[2-(1-methyl-1H-pyrazol-4-yl)-ethyl]-1H-imidazol-5-yl}-benzonitrile
Empirical Formula (Hill Notation):
C20H19N7
CAS Number:
1665195-94-7
Molecular Weight:
357.41
MDL number:
MFCD28166490
UNSPSC Code:
12352200
PubChem Substance ID:
329825762
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

CN(N=C1)C=C1CCN2C=NC(C3=CN(C)N=C3)=C2C4=CC=C(C#N)C=C4

InChI

1S/C20H19N7/c1-25-12-16(10-23-25)7-8-27-14-22-19(18-11-24-26(2)13-18)20(27)17-5-3-15(9-21)4-6-17/h3-6,10-14H,7-8H2,1-2H3

InChI key

RRZVGDGTWNQAPW-UHFFFAOYSA-N

Related Categories

Biochem/physiol Actions

BAZ2-ICR is a chemical probe for BAZ2A/B bromodomains with >100-fold selectivity over other bromodomains, with the exception of CECR2 (15-fold selectivity). BAZ2A is an essential component of the nucleolar remodeling complex (NoRC), which mediates recruitment of histone modifyine enzymes and DNA methylase involved in the silencing of ribosomal RNA transcription by RNA polymerase I. BAZ2B is believed to be involved in regulating nucleosome mobilization along linear DNA. BAZ2-ICR binds to BAZ2A with a KD of 109 nM (ITC) and to BAZ2B with a KD of 170 nM (ITC). BAZ2-ICR also shows accelerated Fluorescence recovery after photobleaching (FRAP) recovery at 1 μM in the BAZ2A FRAP assay. For full characterization details, please visit the BAZ2-ICR probe summary on the Structural Genomics Consortium (SGC) website.

To learn about other SGC chemical probes for epigenetic targets, visit sigma.com/sgc

Features and Benefits

BAZ2-ICR is an epigenetic chemical probe available through a partnership with the Structural Genomics Consortium (SGC). To learn more and view other SGC epigenetic probes, visit sigma.com/SGC.
This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Other Notes

BAZ2-ICR has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the BAZ2-ICR probe summary on the Chemical Probes Portal website.

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Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Samantha M Bevill et al.
Molecular cancer research : MCR, 17(7), 1503-1518 (2019-04-20)
Screening of an inhibitor library targeting kinases and epigenetic regulators identified several molecules having antiproliferative synergy with extraterminal domain (BET) bromodomain (BD) inhibitors (JQ1, OTX015) in triple-negative breast cancer (TNBC). GSK2801, an inhibitor of BAZ2A/B BDs, of the imitation switch
Rodrigo Peña-Hernández et al.
EMBO reports, 22(11), e53014-e53014 (2021-08-18)
Prostate cancer (PCa) is one of the most prevalent cancers in men. Cancer stem cells are thought to be associated with PCa relapse. Here, we show that BAZ2A is required for PCa cells with a cancer stem-like state. BAZ2A genomic

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